The Upper Tribunal decided that Jerome Anderson was guilty of trying to avoid paying tax through a scheme involving investments in the recruitment and training of young footballers at the Bafana Soccer Academy in South Africa.
Anderson used the investment to claim a £3m artificial trading loss, however the Tribunal decided that as his actions were of an investor and not of a trader, he could not do so.
HMRC said this was the first case to consider s74B Income Tax Act 2007, an anti-avoidance provision.
Penny Ciniewicz, HMRC’s director general for customer compliance, said, “The court has made it clear that these schemes don’t work.
“Our public services rely on everyone paying their taxes and it’s unfair for people not to pay their share.
“Anyone who’s caught up in tax avoidance and who wants to put it behind them should come forward now and settle what they owe”.
Anderson represented over 200 footballers during his career as an agent at Sport Entertainment and Media Group. He also represented the boxer Lennox Lewis in his fight against Mike Tyson.